This invention relates to the preparation of organic compounds and more particularly to the preparation of quaternary ammonium salts of hexamethylenetetramine which are useful as microbicides.
These organic quaternary ammonium salts are more specifically designated as 1-methyl-3,5,7-triaza-1-azoniatricyclodecane fluoride, chloride, bromide, and iodide which have the formula (I) ##STR1## wherein X is fluoride, chloride, bromide, or iodide.
Friedrich et al. (Ber. 54B, 1531-42, 1921) have reported the preparation of such compounds, specifically 1-methyl-3,5,7-triaza-1-azoniatricyclodecane chloride, by refluxing a mixture of formaldehyde, ammonium hydroxide and ammonium chloride for 7 hours. As shown in Comparative Example 1, the reaction time for this reaction is unusually long and the yields of the desired product are disadvantageously low.
It is, therefore, a principal object of the present invention to obviate the disadvantages of the prior art processes and to provide an improved process for the preparation of the quarternary ammonium compounds of formula (I).
It is another object of the invention to provide an economical process for the preparation of these compounds as aqueous solutions.
These and other objects and advantages will become apparent as the description proceeds.